Department of Chemistry, Maynooth University, Maynooth, Co., Kildare, Ireland.
Soft Matter. 2020 Sep 14;16(34):7916-7926. doi: 10.1039/d0sm01075h. Epub 2020 Jul 29.
Glycosyl squaramides were synthesised and evaluated as low molecular weight gelators. Amphiphilic glycosyl squaramides 5 and 6, with a C-16 aliphatic chain, formed thermoreversible gels in polar organic solvents and 1 : 1 ethanol/water mixtures with high efficiency. Rheological analysis showed these gels achieve their structural stability 120 h after gelation and were robust, making them particularly suitable for biomedical applications. The interactions between solvent and gelator strongly influence SAFiN (Self-Assembled Fibrillar Network) formation, critical gelation concentration (CGC) and subsequent gel structure, as evidenced by SEM imaging of xerogels. Spectroscopic studies indicate that H-bonding is involved in the self-assembly of the glycosyl squaramides in organic solvents, while hydrophobic interactions are the major driving force for gel formation in the presence of water. The compounds described herein are the first reported examples of carbohydrate-squaramide conjugates capable of forming supramolecular gels.
糖基-squaramide 被合成并评估为低分子量凝胶剂。具有 C-16 脂肪链的两亲性糖基-squaramide 5 和 6 在极性有机溶剂中和 1:1 的乙醇/水混合物中高效形成热可逆凝胶。流变分析表明，这些凝胶在凝胶形成后 120 小时达到结构稳定性，并且坚固，特别适合生物医学应用。溶剂和凝胶剂之间的相互作用强烈影响 SAFiN（自组装纤维网络）的形成、临界凝胶浓度 (CGC) 和随后的凝胶结构，这可以通过干凝胶的 SEM 成像证明。光谱研究表明，氢键参与糖基-squaramide 在有机溶剂中的自组装，而疏水相互作用是在存在水的情况下形成凝胶的主要驱动力。本文所述的化合物是首次报道的能够形成超分子凝胶的碳水化合物-squaramide 缀合物的例子。
